Supplementary Material (ESI) for Organic and Biomolecular Chemistry This journal is (C) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 177 _publ_requested_journal 'Organic & Biomolecular Chemistry' loop_ _publ_author_name 'Benjamin Miller' 'Kevin M. Bucholtz' 'Peter C. Gareiss' 'Stephen G. Tajc' _publ_contact_author_name 'Benjamin Miller' _publ_contact_author_address ; Department of Dermatology University of Rochester Medical Center 601 Elmwood Avenue Box 697 Rochester New York NY-14627-0216 UNITED STATES OF AMERICA ; _publ_contact_author_email BENJAMIN_MILLER@FUTUREHEALTH.ROCHESTER.EDU _publ_section_title ; Synthesis and Evaluation of the First cis-Cyclobutane Containing Receptor for Lipid A ; # Attachment 'KMB_PCG_BLM_OBC_2006_xtal.cif' data_milkb01 _database_code_depnum_ccdc_archive 'CCDC 616053' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common milkb01 _chemical_melting_point ? _chemical_formula_moiety 'C14 H17 N O3' _chemical_formula_sum 'C14 H17 N O3' _chemical_formula_weight 247.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 11.7699(8) _cell_length_b 9.9771(7) _cell_length_c 21.9102(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2572.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 4858 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9831 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_process_details 'SADABS, R. Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10446 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 23.30 _reflns_number_total 1909 _reflns_number_gt 1520 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker' _computing_cell_refinement 'SAINT, Bruker' _computing_data_reduction 'SAINT, Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1127P)^2^+0.3543P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? #_refine_ls_abs_structure_details # 'Flack H D (1983), 921 Friedel pairs, Acta Cryst. A39, 876-881' #_refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 1909 _refine_ls_number_parameters 325 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1608 _refine_ls_wR_factor_gt 0.1521 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O11 O 0.2762(3) 0.7344(4) 0.8195(2) 0.0458(11) Uani 1 1 d . . . H11C H 0.2957 0.8095 0.8334 0.069 Uiso 1 1 calc R . . O21 O 0.4602(3) 0.6878(4) 0.8337(2) 0.0495(12) Uani 1 1 d . . . O31 O 0.2996(3) 0.5333(4) 0.92354(18) 0.0403(11) Uani 1 1 d . . . N11 N 0.1293(5) 0.4324(7) 0.9185(2) 0.0629(18) Uani 1 1 d . . . H11B H 0.0783 0.3932 0.8952 0.075 Uiso 1 1 calc R . . C11 C 0.3652(5) 0.6532(6) 0.8187(3) 0.0382(14) Uani 1 1 d . . . C21 C 0.3354(6) 0.5176(6) 0.7945(3) 0.0505(17) Uani 1 1 d . . . H21A H 0.3141 0.5265 0.7505 0.061 Uiso 1 1 calc R . . C31 C 0.4163(6) 0.4016(7) 0.8012(4) 0.069(2) Uani 1 1 d . . . H31A H 0.4543 0.3759 0.7626 0.083 Uiso 1 1 calc R . . H31B H 0.4725 0.4134 0.8344 0.083 Uiso 1 1 calc R . . C41 C 0.3191(7) 0.3124(7) 0.8180(5) 0.076(2) Uani 1 1 d . . . H41A H 0.3323 0.2599 0.8557 0.092 Uiso 1 1 calc R . . H41B H 0.2937 0.2535 0.7843 0.092 Uiso 1 1 calc R . . C51 C 0.2419(5) 0.4368(6) 0.8277(3) 0.0467(16) Uani 1 1 d . . . H51A H 0.1692 0.4320 0.8042 0.056 Uiso 1 1 calc R . . C61 C 0.2247(5) 0.4736(6) 0.8941(3) 0.0391(15) Uani 1 1 d . . . C71 C 0.1056(6) 0.4499(7) 0.9834(3) 0.0596(18) Uani 1 1 d . . . H71A H 0.1775 0.4567 1.0066 0.071 Uiso 1 1 calc R . . H71B H 0.0621 0.3723 0.9992 0.071 Uiso 1 1 calc R . . C81 C 0.0391(5) 0.5734(8) 0.9905(4) 0.065(2) Uani 1 1 d . . . H81A H -0.0308 0.5679 0.9655 0.078 Uiso 1 1 calc R . . H81B H 0.0841 0.6511 0.9761 0.078 Uiso 1 1 calc R . . C91 C 0.0068(6) 0.5931(9) 1.0597(3) 0.065(2) Uani 1 1 d . . . C101 C -0.0945(6) 0.5469(8) 1.0830(3) 0.0582(19) Uani 1 1 d . . . H10A H -0.1406 0.4896 1.0588 0.070 Uiso 1 1 calc R . . C111 C -0.1300(7) 0.5811(9) 1.1396(3) 0.066(2) Uani 1 1 d . . . H11A H -0.2033 0.5548 1.1531 0.079 Uiso 1 1 calc R . . C121 C -0.0620(9) 0.6522(9) 1.1767(4) 0.089(3) Uani 1 1 d . . . H12A H -0.0876 0.6760 1.2163 0.106 Uiso 1 1 calc R . . C131 C 0.0444(7) 0.6907(8) 1.1576(3) 0.067(2) Uani 1 1 d . . . H13A H 0.0934 0.7383 1.1844 0.080 Uiso 1 1 calc R . . C141 C 0.0791(6) 0.6597(8) 1.0996(4) 0.067(2) Uani 1 1 d . . . H14A H 0.1533 0.6841 1.0865 0.080 Uiso 1 1 calc R . . O12 O 0.4526(3) 0.8293(4) 0.97887(19) 0.0479(11) Uani 1 1 d . . . O22 O 0.2739(3) 0.7580(4) 0.9869(2) 0.0500(12) Uani 1 1 d . . . H22B H 0.3010 0.6884 0.9710 0.075 Uiso 1 1 calc R . . O32 O 0.2901(3) 0.9589(4) 0.88231(18) 0.0446(11) Uani 1 1 d . . . N12 N 0.1084(5) 1.0191(6) 0.8969(3) 0.0569(16) Uani 1 1 d . . . H12C H 0.0621 1.0676 0.9193 0.068 Uiso 1 1 calc R . . C12 C 0.3552(6) 0.8484(6) 0.9934(3) 0.0428(15) Uani 1 1 d . . . C22 C 0.3063(6) 0.9734(6) 1.0213(3) 0.0556(18) Uani 1 1 d . . . H22A H 0.2571 0.9518 1.0572 0.067 Uiso 1 1 calc R . . C32 C 0.3878(7) 1.0864(7) 1.0358(4) 0.073(2) Uani 1 1 d . . . H32A H 0.3715 1.1325 1.0748 0.088 Uiso 1 1 calc R . . H32B H 0.4689 1.0605 1.0331 0.088 Uiso 1 1 calc R . . C42 C 0.3446(6) 1.1603(7) 0.9803(4) 0.069(2) Uani 1 1 d . . . H42A H 0.3239 1.2547 0.9888 0.083 Uiso 1 1 calc R . . H42B H 0.3965 1.1546 0.9448 0.083 Uiso 1 1 calc R . . C52 C 0.2434(6) 1.0690(6) 0.9753(3) 0.0463(16) Uani 1 1 d . . . H52A H 0.1749 1.1103 0.9946 0.056 Uiso 1 1 calc R . . C62 C 0.2154(5) 1.0133(5) 0.9138(3) 0.0383(15) Uani 1 1 d . . . C72 C 0.0586(5) 0.9493(7) 0.8420(3) 0.0597(19) Uani 1 1 d . . . H72A H 0.0898 0.8574 0.8393 0.072 Uiso 1 1 calc R . . H72B H -0.0248 0.9422 0.8470 0.072 Uiso 1 1 calc R . . C82 C 0.0848(5) 1.0239(6) 0.7841(3) 0.0554(17) Uani 1 1 d . . . H82A H 0.1679 1.0297 0.7778 0.066 Uiso 1 1 calc R . . H82B H 0.0535 1.1160 0.7859 0.066 Uiso 1 1 calc R . . C92 C 0.0292(6) 0.9448(8) 0.7323(3) 0.0608(19) Uani 1 1 d . . . C102 C -0.0865(6) 0.9642(7) 0.7200(3) 0.0597(19) Uani 1 1 d . . . H10B H -0.1305 1.0201 0.7459 0.072 Uiso 1 1 calc R . . C112 C -0.1362(7) 0.9037(9) 0.6711(4) 0.076(3) Uani 1 1 d . . . H11D H -0.2140 0.9199 0.6621 0.091 Uiso 1 1 calc R . . C122 C -0.0725(10) 0.8179(9) 0.6344(4) 0.089(3) Uani 1 1 d . . . H12B H -0.1063 0.7778 0.5995 0.107 Uiso 1 1 calc R . . C132 C 0.0388(8) 0.7909(8) 0.6482(3) 0.074(2) Uani 1 1 d . . . H13B H 0.0810 0.7286 0.6245 0.089 Uiso 1 1 calc R . . C142 C 0.0886(7) 0.8556(8) 0.6973(4) 0.069(2) Uani 1 1 d . . . H14B H 0.1658 0.8378 0.7068 0.083 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O11 0.046(2) 0.037(2) 0.055(3) -0.006(2) -0.005(2) 0.0075(19) O21 0.045(3) 0.047(3) 0.056(3) 0.008(2) 0.008(2) 0.006(2) O31 0.036(2) 0.040(2) 0.045(2) 0.001(2) -0.0074(19) -0.0003(19) N11 0.053(3) 0.093(5) 0.043(3) -0.026(3) 0.017(3) -0.033(3) C11 0.051(4) 0.036(3) 0.028(3) 0.001(3) 0.010(3) 0.003(3) C21 0.080(4) 0.032(3) 0.039(4) -0.004(3) 0.022(3) 0.002(3) C31 0.061(4) 0.045(4) 0.100(6) -0.022(4) 0.028(4) 0.002(3) C41 0.102(5) 0.043(4) 0.084(6) -0.001(4) 0.035(5) 0.011(4) C51 0.043(3) 0.038(3) 0.059(4) -0.017(3) 0.010(3) -0.003(3) C61 0.037(3) 0.038(3) 0.042(3) -0.004(3) -0.008(3) 0.008(3) C71 0.055(4) 0.055(4) 0.069(5) 0.003(4) 0.004(4) 0.001(3) C81 0.042(4) 0.069(5) 0.083(5) 0.028(4) -0.024(4) -0.008(3) C91 0.056(4) 0.096(6) 0.043(4) -0.037(4) 0.009(3) -0.015(4) C101 0.049(4) 0.076(5) 0.049(4) -0.008(4) 0.008(3) -0.010(4) C111 0.076(5) 0.071(5) 0.051(5) 0.002(4) 0.021(4) -0.006(4) C121 0.136(8) 0.081(6) 0.049(5) -0.012(5) 0.032(5) -0.011(6) C131 0.102(7) 0.058(5) 0.040(4) -0.004(4) -0.014(4) -0.001(4) C141 0.056(4) 0.085(5) 0.059(5) -0.029(4) 0.002(4) -0.012(4) O12 0.043(3) 0.049(3) 0.052(3) 0.012(2) -0.007(2) -0.013(2) O22 0.047(3) 0.040(2) 0.063(3) -0.010(2) 0.009(2) -0.007(2) O32 0.051(3) 0.038(2) 0.045(2) -0.008(2) 0.004(2) 0.007(2) N12 0.053(3) 0.069(4) 0.048(3) -0.022(3) -0.008(3) 0.024(3) C12 0.056(4) 0.035(3) 0.038(4) 0.007(3) -0.014(3) -0.004(3) C22 0.077(5) 0.044(4) 0.046(4) -0.001(3) 0.001(3) -0.012(3) C32 0.089(5) 0.050(4) 0.081(6) -0.015(4) -0.035(4) 0.003(4) C42 0.084(5) 0.056(5) 0.067(5) -0.002(4) -0.016(4) -0.021(4) C52 0.048(3) 0.038(3) 0.053(4) -0.018(3) -0.004(3) 0.014(3) C62 0.051(4) 0.025(3) 0.040(4) -0.004(3) 0.003(3) 0.012(3) C72 0.045(4) 0.062(4) 0.072(5) 0.005(4) 0.013(3) 0.014(3) C82 0.050(4) 0.044(4) 0.072(4) 0.007(4) 0.005(4) -0.003(3) C92 0.051(4) 0.077(5) 0.055(4) -0.020(4) -0.011(3) 0.014(3) C102 0.063(5) 0.061(4) 0.054(4) -0.008(4) -0.003(4) 0.001(4) C112 0.078(5) 0.091(6) 0.058(5) 0.016(5) -0.019(4) -0.023(5) C122 0.142(9) 0.088(7) 0.037(5) -0.011(4) -0.019(5) -0.008(6) C132 0.113(8) 0.065(5) 0.044(5) -0.009(4) 0.012(5) 0.017(5) C142 0.069(5) 0.068(5) 0.069(5) -0.011(4) 0.010(4) 0.011(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O11 C11 1.325(7) . ? O11 H11C 0.8400 . ? O21 C11 1.216(7) . ? O31 C61 1.244(7) . ? N11 C61 1.310(8) . ? N11 C71 1.461(9) . ? N11 H11B 0.8800 . ? C11 C21 1.494(9) . ? C21 C31 1.506(10) . ? C21 C51 1.546(8) . ? C21 H21A 1.0000 . ? C31 C41 1.495(10) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C41 C51 1.552(9) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C51 C61 1.514(9) . ? C51 H51A 1.0000 . ? C71 C81 1.468(10) . ? C71 H71A 0.9900 . ? C71 H71B 0.9900 . ? C81 C91 1.576(11) . ? C81 H81A 0.9900 . ? C81 H81B 0.9900 . ? C91 C101 1.376(10) . ? C91 C141 1.390(10) . ? C101 C111 1.351(10) . ? C101 H10A 0.9500 . ? C111 C121 1.343(12) . ? C111 H11A 0.9500 . ? C121 C131 1.375(12) . ? C121 H12A 0.9500 . ? C131 C141 1.370(11) . ? C131 H13A 0.9500 . ? C141 H14A 0.9500 . ? O12 C12 1.206(7) . ? O22 C12 1.322(7) . ? O22 H22B 0.8400 . ? O32 C62 1.243(6) . ? N12 C62 1.315(8) . ? N12 C72 1.507(9) . ? N12 H12C 0.8800 . ? C12 C22 1.504(9) . ? C22 C32 1.514(10) . ? C22 C52 1.573(9) . ? C22 H22A 1.0000 . ? C32 C42 1.510(11) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C42 C52 1.503(9) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C52 C62 1.493(8) . ? C52 H52A 1.0000 . ? C72 C82 1.503(9) . ? C72 H72A 0.9900 . ? C72 H72B 0.9900 . ? C82 C92 1.530(10) . ? C82 H82A 0.9900 . ? C82 H82B 0.9900 . ? C92 C142 1.368(10) . ? C92 C102 1.401(10) . ? C102 C112 1.361(10) . ? C102 H10B 0.9500 . ? C112 C122 1.395(12) . ? C112 H11D 0.9500 . ? C122 C132 1.371(12) . ? C122 H12B 0.9500 . ? C132 C142 1.384(11) . ? C132 H13B 0.9500 . ? C142 H14B 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O11 H11C 109.5 . . ? C61 N11 C71 121.6(5) . . ? C61 N11 H11B 119.2 . . ? C71 N11 H11B 119.2 . . ? O21 C11 O11 123.4(5) . . ? O21 C11 C21 124.7(6) . . ? O11 C11 C21 111.9(6) . . ? C11 C21 C31 120.9(6) . . ? C11 C21 C51 118.2(5) . . ? C31 C21 C51 90.2(5) . . ? C11 C21 H21A 108.7 . . ? C31 C21 H21A 108.7 . . ? C51 C21 H21A 108.7 . . ? C41 C31 C21 89.9(5) . . ? C41 C31 H31A 113.7 . . ? C21 C31 H31A 113.7 . . ? C41 C31 H31B 113.7 . . ? C21 C31 H31B 113.7 . . ? H31A C31 H31B 110.9 . . ? C31 C41 C51 90.3(5) . . ? C31 C41 H41A 113.6 . . ? C51 C41 H41A 113.6 . . ? C31 C41 H41B 113.6 . . ? C51 C41 H41B 113.6 . . ? H41A C41 H41B 110.9 . . ? C61 C51 C21 114.8(5) . . ? C61 C51 C41 113.8(6) . . ? C21 C51 C41 86.4(5) . . ? C61 C51 H51A 113.1 . . ? C21 C51 H51A 113.1 . . ? C41 C51 H51A 113.1 . . ? O31 C61 N11 123.1(6) . . ? O31 C61 C51 121.3(6) . . ? N11 C61 C51 115.5(5) . . ? N11 C71 C81 107.7(6) . . ? N11 C71 H71A 110.2 . . ? C81 C71 H71A 110.2 . . ? N11 C71 H71B 110.2 . . ? C81 C71 H71B 110.2 . . ? H71A C71 H71B 108.5 . . ? C71 C81 C91 109.5(6) . . ? C71 C81 H81A 109.8 . . ? C91 C81 H81A 109.8 . . ? C71 C81 H81B 109.8 . . ? C91 C81 H81B 109.8 . . ? H81A C81 H81B 108.2 . . ? C101 C91 C141 117.2(7) . . ? C101 C91 C81 121.7(6) . . ? C141 C91 C81 121.1(7) . . ? C111 C101 C91 121.6(7) . . ? C111 C101 H10A 119.2 . . ? C91 C101 H10A 119.2 . . ? C121 C111 C101 120.3(8) . . ? C121 C111 H11A 119.9 . . ? C101 C111 H11A 119.9 . . ? C111 C121 C131 120.4(7) . . ? C111 C121 H12A 119.8 . . ? C131 C121 H12A 119.8 . . ? C141 C131 C121 119.3(7) . . ? C141 C131 H13A 120.3 . . ? C121 C131 H13A 120.3 . . ? C131 C141 C91 120.6(7) . . ? C131 C141 H14A 119.7 . . ? C91 C141 H14A 119.7 . . ? C12 O22 H22B 109.5 . . ? C62 N12 C72 125.3(5) . . ? C62 N12 H12C 117.3 . . ? C72 N12 H12C 117.3 . . ? O12 C12 O22 123.6(6) . . ? O12 C12 C22 127.0(6) . . ? O22 C12 C22 109.4(6) . . ? C12 C22 C32 117.4(6) . . ? C12 C22 C52 114.9(5) . . ? C32 C22 C52 88.9(5) . . ? C12 C22 H22A 111.3 . . ? C32 C22 H22A 111.3 . . ? C52 C22 H22A 111.3 . . ? C42 C32 C22 88.9(5) . . ? C42 C32 H32A 113.8 . . ? C22 C32 H32A 113.8 . . ? C42 C32 H32B 113.8 . . ? C22 C32 H32B 113.8 . . ? H32A C32 H32B 111.1 . . ? C52 C42 C32 91.7(6) . . ? C52 C42 H42A 113.3 . . ? C32 C42 H42A 113.3 . . ? C52 C42 H42B 113.3 . . ? C32 C42 H42B 113.3 . . ? H42A C42 H42B 110.7 . . ? C62 C52 C42 117.8(7) . . ? C62 C52 C22 117.2(5) . . ? C42 C52 C22 87.0(5) . . ? C62 C52 H52A 110.9 . . ? C42 C52 H52A 110.9 . . ? C22 C52 H52A 110.9 . . ? O32 C62 N12 122.6(5) . . ? O32 C62 C52 120.5(6) . . ? N12 C62 C52 116.8(6) . . ? C82 C72 N12 111.4(6) . . ? C82 C72 H72A 109.4 . . ? N12 C72 H72A 109.4 . . ? C82 C72 H72B 109.4 . . ? N12 C72 H72B 109.4 . . ? H72A C72 H72B 108.0 . . ? C72 C82 C92 106.4(5) . . ? C72 C82 H82A 110.4 . . ? C92 C82 H82A 110.4 . . ? C72 C82 H82B 110.4 . . ? C92 C82 H82B 110.4 . . ? H82A C82 H82B 108.6 . . ? C142 C92 C102 118.6(7) . . ? C142 C92 C82 122.3(6) . . ? C102 C92 C82 119.2(6) . . ? C112 C102 C92 120.6(8) . . ? C112 C102 H10B 119.7 . . ? C92 C102 H10B 119.7 . . ? C102 C112 C122 119.7(8) . . ? C102 C112 H11D 120.2 . . ? C122 C112 H11D 120.2 . . ? C132 C122 C112 120.4(8) . . ? C132 C122 H12B 119.8 . . ? C112 C122 H12B 119.8 . . ? C122 C132 C142 119.0(8) . . ? C122 C132 H13B 120.5 . . ? C142 C132 H13B 120.5 . . ? C92 C142 C132 121.5(8) . . ? C92 C142 H14B 119.2 . . ? C132 C142 H14B 119.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O21 C11 C21 C31 15.4(10) . . . . ? O11 C11 C21 C31 -167.6(6) . . . . ? O21 C11 C21 C51 124.3(7) . . . . ? O11 C11 C21 C51 -58.7(7) . . . . ? C11 C21 C31 C41 137.4(6) . . . . ? C51 C21 C31 C41 13.9(6) . . . . ? C21 C31 C41 C51 -13.8(6) . . . . ? C11 C21 C51 C61 -24.5(8) . . . . ? C31 C21 C51 C61 101.2(6) . . . . ? C11 C21 C51 C41 -139.1(7) . . . . ? C31 C21 C51 C41 -13.4(6) . . . . ? C31 C41 C51 C61 -102.1(7) . . . . ? C31 C41 C51 C21 13.5(6) . . . . ? C71 N11 C61 O31 -2.2(10) . . . . ? C71 N11 C61 C51 174.4(6) . . . . ? C21 C51 C61 O31 -19.9(8) . . . . ? C41 C51 C61 O31 77.4(7) . . . . ? C21 C51 C61 N11 163.4(6) . . . . ? C41 C51 C61 N11 -99.2(7) . . . . ? C61 N11 C71 C81 95.4(8) . . . . ? N11 C71 C81 C91 177.5(5) . . . . ? C71 C81 C91 C101 -93.2(9) . . . . ? C71 C81 C91 C141 87.8(9) . . . . ? C141 C91 C101 C111 9.3(13) . . . . ? C81 C91 C101 C111 -169.8(8) . . . . ? C91 C101 C111 C121 -5.8(13) . . . . ? C101 C111 C121 C131 -0.1(14) . . . . ? C111 C121 C131 C141 2.2(14) . . . . ? C121 C131 C141 C91 1.6(13) . . . . ? C101 C91 C141 C131 -7.1(13) . . . . ? C81 C91 C141 C131 171.9(7) . . . . ? O12 C12 C22 C32 -3.0(10) . . . . ? O22 C12 C22 C32 176.6(6) . . . . ? O12 C12 C22 C52 99.6(8) . . . . ? O22 C12 C22 C52 -80.9(7) . . . . ? C12 C22 C32 C42 104.0(6) . . . . ? C52 C22 C32 C42 -13.7(6) . . . . ? C22 C32 C42 C52 14.4(6) . . . . ? C32 C42 C52 C62 -133.2(6) . . . . ? C32 C42 C52 C22 -13.8(6) . . . . ? C12 C22 C52 C62 13.8(9) . . . . ? C32 C22 C52 C62 133.7(7) . . . . ? C12 C22 C52 C42 -106.1(6) . . . . ? C32 C22 C52 C42 13.8(6) . . . . ? C72 N12 C62 O32 7.2(10) . . . . ? C72 N12 C62 C52 -169.3(6) . . . . ? C42 C52 C62 O32 49.9(8) . . . . ? C22 C52 C62 O32 -51.9(8) . . . . ? C42 C52 C62 N12 -133.4(7) . . . . ? C22 C52 C62 N12 124.7(7) . . . . ? C62 N12 C72 C82 -78.8(8) . . . . ? N12 C72 C82 C92 -179.4(5) . . . . ? C72 C82 C92 C142 -97.5(8) . . . . ? C72 C82 C92 C102 82.8(8) . . . . ? C142 C92 C102 C112 -5.1(12) . . . . ? C82 C92 C102 C112 174.6(6) . . . . ? C92 C102 C112 C122 2.3(12) . . . . ? C102 C112 C122 C132 2.1(13) . . . . ? C112 C122 C132 C142 -3.5(13) . . . . ? C102 C92 C142 C132 3.7(12) . . . . ? C82 C92 C142 C132 -176.0(8) . . . . ? C122 C132 C142 C92 0.5(13) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 23.30 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.398 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.051